Title

Porphyrin-Piperidine Hybrids: Hosts for Chiral Guest Recognition

Author

Xiaowen Wu

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2013

Abstract

The aim of this project is to develop chiral porphyrin compounds that can serve as synthetic receptors for the selective binding of chiral anions and chiral amines. The main approach to our objective of developing chiral porphyrin compounds was the attachment of piperidine derivatives to one of the meso positions of tetraphenyl porphyrin. The research included the synthesis and study of the recognition properties of the chiral porphyrin-based receptors. Additionally, recognition properties of a non-chiral porphyrin receptor are reported as a model for our hosts. The key structural component of the synthetic receptors synthesized centers on the functionalization of one meso position with a chiral anion recognition moiety such that a hydrogen bond donating group projects over the surface of the porphyin; thus the hosts contain an introverted hydrogen bond donating group. Metallation of the porphyrin provides an additional binding site. The introverted hydrogen bond donating group works in collaboration with the metallo site in guest binging. Recognition properties of the host with different chiral guests such as amino acid derivatives, carboxylates and amines are reported in this thesis. The recognition studies were conducted using Uv/Vis and NMR titrations. The results reveal some of the major factors contributing to the ability of porphyrin-based hosts to bind with chiral guests stereoselectively.

Advisor

Stephen Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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